IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

The impact of different yeasts and harvest time on the wine quality of Beihong and Beimei (<I>V. vinifera x V. amurensis</I>)

Beihong and Beimei are two wine cultivars from ‘Muscat Hamberg’ (V. vinifera L.) and wild V. amurensis Rupr., which were released in China in 2008. Here，two enology practices were reported. Firstly, the impact of different yeasts including D254, GRE, K1, D21 and BDX on dry wine quality of Beihong and Beimei was investigated. For Beihong, among wines fermented by all yeasts, residual sugar content was the lowest, total anthocyanin and resveratrol contents were the highest in the wine by D254. However, the wine by D254 had lower titrable acid than those by the other yeasts except BDX.

Read More

Classification of the wine-growing environment of Central Mancha (Spain). First works

This paper describes a zoning study performed on a vast territory of around 86,500 hectares, situated in the countryside area of La Mancha Central (Castilla-La Mancha). The aim of the study was to classify the environment according to a small number of ecological criteria, establish the relevant territorial units and generate thematic maps with the different levels of criteria employed and synthetic maps by crossing these criteria.

Read More

The use of remote sensing for intra-block vineyard management

L’unité de gestion technique d’un vignoble est aujourd’hui la parcelle. Néanmoins, au sein d’une même parcelle, la variabilité de l’expression végétative et de la constitution des raisins à maturité, peut être grande, en particulier à cause d’une hétérogénéité du sol.

Read More

The origin and the discovery of “terroir”

Le mot “terroir” dérive du latin “terra”, mais déjà les Romains l’indiquaient comme “locus” ou”loci”, c’est-à-dire un lieu ayant le “genius”destiné à la production d’un produit d’excellente qualité.

Read More

A pragmatic modeling approach to assessing vine water status

Climate change scenarios suggest an increase in temperatures and an intensification of summer drought. Measuring seasonal plant water status is an essential step in choosing appropriate adaptations to ensure yields and quality of agricultural produce. The water status of grapevines is known to be a key factor for yield, maturity of grapes and wine quality. Several techniques exist to measure the water status of soil and plants, but stem water potential proved to be a simple and precise tool for different plant species.

Read More